Methoxymethylmenthol.



, UNITED STATES PATENT OFFICE.

MAX DOHRN AND ALBRECHT THIELE, OF BERLIN, GERMANY, ASSIGNORS 'IO CHE- MISCHE FABRIK A UF ACTIEN (VORM. E. SCHERING), 0F BERLIN, GERMANY.

METH OXYMETHYLM EN THOL.

Specification of Letters Patent. Application filed February 15, 1911. Serial atu-re gradually added to 1 molecule of menthol sodium suspended 111 toluene. The ad dition takes place while Stlll'lllg' WlllCll 1s contlnued for some hours; after standing for about 24hours the mother liquor is remoy'ed The toluene after purification No Drawing. N 0. 608,698.

To all whom it may concern:

Be it known that we, MAX DOHRN and ALBRECHT THIELE, doctors of philosophy, chemists, citizens of the German Empire, re- Berlin, Kingdom of Prussia, Gerslding at man Emp1re,'have invented a new and use- .ful Improvement 111 the Product-ion of of the filtrate in vacuo is distilled oil and thelllethoxymethylmenthol, of which the folresiduum reactionated. lowing is a specification. We claim as our invention:

ur invention relates to the manufacture The herein described new methoxymethylof the hitherto unknown methoxymethylmentho corresponding to the formula menthol being a valuable pharmaceutical C H OOI-I OCH beinga colorless liquid product. T e new compound corresponds oiling at 7 millimeter pressure at about to theformula C, H ,.OOH .O and is a from 100 to 102 centigrade, insoluble in colorless liquid boiling at 7 millimeter pressure at about from 100 to 102 centigrade. The liquid which has a menthol like smell is insoluble in water, soluble in organic solvents and splits off formaldehyde on heating h mineral acids. The methoxymethylmenthol is :obtained a menthol like smell, liberating formaldehyde on heating with mineral acids, and being a valuable therapeutic compound, substantially as described.

In testimony whereof we have hereunto set our signatures in the presence of tWo by reacting with chlormethylet-her upon subscribing witnesses. menthol in the presence of a condensing; MAX DOHRN. agent. or upon an alkali salt of menthol. In ALBRECHT THIELE. carrying-out our process practicallywe pro- Witnesses: oeed, for instance, as follows: 2 molecules HENRY HAsPER,

are at ordinary temperof chlormethylether VVoLnnM'AR HAUrr.

Patented June 6, 1911..

Water, soluble in organic solvents, having 

